The phrase "lucky stiff" is a slang and somewhat dated expression meaning an exceptionally lucky person. It often carries connotations of jealousy or contempt toward the person considered lucky.

Additionally, "Lucky Stiff" is also the title of a musical farce that debuted off-Broadway in 1988, based on a novel, involving a quirky plot about inheriting a fortune under unusual conditions. But in common usage, "lucky stiff" simply refers to someone who is very lucky.